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Synthesis 1993; 1993(12): 1243-1246
DOI: 10.1055/s-1993-26035
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Use of N,N′-Dimethylpropyleneurea (DMPU) as Solvent in the Efficient Preparation of Enantiomerically Pure Secondary Amines

Eusebio Juaristi* , Peter Murer, Dieter Seebach
  • *Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule, ETH-Zentrum, Universitätsstraße 16, CH-8092 Zürich, Switzerland
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Publication Date:
29 April 2002 (online)

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The monoalkylation of (R)- and (S)-1-phenylethylamine proceeds readily with DMPU as the solvent. An efficient procedure was then developed for the high-yield preparation of the chiral secondary amines N-benzyl-, N-isopropyl-, N-(2-biphenylyl)methyl-, N-(diphenyl)methyl-, and N-(2,2-dimethyl)propyl-1-phenylethylamine, in enantiomerically pure form.